Carpooling (also referred to, for example, as car-sharing or ride-sharing) refers to the sharing of vehicle journeys such that more than one just person travels in a vehicle towards one or more destinations. By having multiple people using one vehicle, carpooling can reduce each person's travel costs, such as fuel cost, tolls, etc., as well as potentially reduce stress related to driving. Existing carpooling technology, however, commonly fails to account for, and/or encompass, participant variables such as, for example, driver skill with respect to various landscapes, as well as anomalous driver behavior.